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Application of Sulfuryl Chloride for the Quick Construction of β-Chlorotetrahydrofuran Derivatives from Homoallylic Alcohols under Mild Conditions

Xianghua Zeng, Chengxia Miao, Shoufeng Wang, Chungu Xia, Wei Sun*

*State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, P. R. of China, Email: wsunlicp.cas.cn

X. Zeng, C. Miao, S. Wang, C. Xia, W. Sun, Synthesis, 2013, 45, 2391-2396.

DOI: 10.1055/s-0033-1339351



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Abstract

Sulfuryl chloride as chlorinating agent enables an efficient, mild and catalyst-free synthesis of β-chlorotetrahydrofuran derivatives by 5-endo chlorocycloetherification of homoallylic alcohols. A variety of homoallylic alcohols with aryl or alkyl substituents were smoothly converted into β-chlorotetrahydrofurans in very good yields.

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Key Words

homoallylic alcohols, sulfuryl chloride, 5-endo cyclization, tetrahydrofurans


ID: J66-Y2013